Catalytic Enantioselective Arylation of N-Tosylarylimines with Arylboronic Acids Using C₂-Symmetric Cationic N-Heterocyclic Carbene Pd²⁺ Diaquo Complexes

Guang-Ning Ma, Tao Zhang and Min Shi*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China, Email: mshimail.sioc.ac.cn

G.-N. Ma, T. Zhang, M. Shi, Org. Lett., 2009, 11, 875-878.

DOI: 10.1021/ol802861s

Abstract

An asymmetric arylation of N-tosylimines with arylboronic acids was realized by using a chiral cationic C₂-symmetric N-heterocyclic carbene Pd²⁺ diaquo complex as catalyst in combination with K₃PO₄ • 3 H₂O in THF at 4°C in the presence of powdered 4 Å MS to afford the corresponding adducts in excellent yields and good enantioselectivities.

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Key Words

Benzylamines

ID: J54-Y2009-0520

Catalytic Enantioselective Arylation of N-Tosylarylimines with Arylboronic Acids Using C2-Symmetric Cationic N-Heterocyclic Carbene Pd2+ Diaquo Complexes

Guang-Ning Ma, Tao Zhang and Min Shi*

Catalytic Enantioselective Arylation of N-Tosylarylimines with Arylboronic Acids Using C₂-Symmetric Cationic N-Heterocyclic Carbene Pd²⁺ Diaquo Complexes